The Best Chicago Neighborhoods for Food, History, Comedy, and More

BY: Groupon Editors |Nov 27, 2017

As soon as you set foot in Chicago, it becomes clear that this is a city built on its neighborhoods. From Hyde Park and Bronzeville in the south to Lincoln Square and Lakeview in the north, each one offers unique things to see, eat, and do. This variety can make a weekend in the city almost intimidating: it's no easy task to narrow down a list of what to do in Chicago and its many tempting enclaves. To help, we've detailed the best Chicago neighborhoods for eating, history, architecture, and more.

Best Neighborhood for Foodies: Fulton Market

You can get deep dish, hot dogs, and Italian beef anywhere in Chicago. But what you can't get in any of the Chicago neighborhoods—or just about anywhere else in the country—is the incredible selection of world-class eats in Fulton Market. From Michelin-starred options (Roister, Oriole, and Blackbird, to name a few) to celebrity-chef hotspots (Rick Bayless's Leña Brava and Stephanie Izard's Girl & the Goat) to homages to Chicago's history as a meatpacking hub (Green Street Smoked Meats and The Publican), Fulton Market is a food lover's paradise.

  • What to Do: Earn your next big meal with a calorie- and stress-burning session of axe throwing at Bad Axe Throwing. Groups and individuals can embrace their inner lumberjack while tossing razor-sharp axes at wooden bull's eyes.

  • Where to Eat: It might take making a reservation months in advance, but a dinner at Girl & the Goat is worth it. The braised pork shank (served with a buttermilk dressing, naan, and squash-mushroom kimchi) is one of the best dishes in the entire city.

  • Where to Stay: A little over a mile from Fulton Market sits the Kinzie Hotel (from $56/night), and a walk between the two locales takes you past The Doughnut Vault, home to some of the best donuts in Chicago.

Best Neighborhood for History Buffs: Bridgeport

Chicago is a town teeming with history in any of its neighborhoods, but Bridgeport is where you should head if you really want to dive into the city's past. In the south end of the neighborhood, you can snap an Instagram-worthy pic of the gate to the Union Stockyards, which served as the hub of the American meatpacking industry for decades in the late 1800s and early 1900s. Palmisano Park occupies space where there was once an ancient coral reef. (It was eventually turned into a limestone quarry.) And for a truly old-school Chicago experience, you can grab a beer at Shinnick's Pub, a 79-year-old institution that's been in the Shinnick family for four generations.

  • What to Do: Visit the Chicago Maritime Museum, where you can learn about the city's history in relationship to its river, the Great Lakes, and its role as a shipping hub through more than 10,000 artifacts.

  • Where to Eat: When you're making a list of where to eat in Chicago, Ricobene's is a must. Their signature breaded-steak sandwich—fried steak bathed in a zesty tomato sauce and covered in mozzarella—is the best in the city and a local gastronomic icon.

  • Where to Stay: While it's not in Bridgeport, The Drake (from $55/night) is one of the most historic hotels in Chicago. A member of the Historic Hotels of America program, the hotel has hosted the likes of Bing Crosby, Walt Disney, Marilyn Monroe, and George Gershwin since its 1920 opening.

Best Neighborhood for Architecture Geeks: The Loop

The Chicago skyline is one of the most recognizable on the planet, and The Loop—the neighborhood in the heart of the city's downtown area—is where you'll find the majority of the architectural wonders that make it up. Along with a dizzying number of iconic skyscrapers, The Loop is home to the propped-up tracks of the El, the drawbridges spanning the Chicago River, and the two-tiered (and notoriously difficult to navigate) Wacker Drive.

  • What to Do: Go on a walking tour dedicated to art deco, the architectural style that dominates Chicago's skyline. Once you're done gawking at the Board of Trade Building and the gold-tipped Carbide & Carbon Building, test your bravery at the Willis Tower's Skydeck, where only a clear glass floor separates you from 1,353 feet of air.

  • Where to Eat: Revival Food Hall takes some of the best restaurants in Chicago and puts them all under the same roof. In the huge cafeteria, you can grab Detroit-style pizza from Union Squared, brisket sandwiches from Smoque BBQ, hot chicken from The Budlong, and more.

  • Where to Stay: Get a room in the middle of The Loop's grid at the Hampton Inn Majestic Chicago (from $71/night), an 18-story beaux arts skyscraper that also houses the CIBC (originally Majestic) Theatre.

Best Neighborhood for Nature Lovers: Lincoln Park

You might not expect a neighborhood just a couple miles north of downtown to be a nature lover's dream, but that's what you'll find in Lincoln Park. There's the eponymous park, first of all: a 1,200-acre lakeside expanse with pedestrian trails, sports fields, a conservatory, a nature museum, and a free zoo. There's also Oz Park, a green space with picnic-worthy shade, a massive playground, and statues of Dorothy and her Wizard of Oz companions. Finally, the endless leafy residential avenues packed with tidy row homes make for picture-perfect weekend strolls.

  • What to Do: Spend an afternoon at the Lincoln Park Zoo, which is open 365 days a year and completely free to enter. Top exhibits include the primate house, home to gorillas, gibbons, and monkeys; and the brand-new Walter Family Arctic Tundra, which houses the zoo's polar bears.

  • Where to Eat: For a different take on pizza, go to the Chicago Pizza & Oven Grinder Co., where instead of a traditional slice, you'll get a giant pot pie filled with cheese, sauce, sausage, and a doorknob-sized mushroom. Note that it's cash only, it's very popular, and they don't take reservations, so expect a wait.

  • Where to Stay: The Hotel Lincoln (from $77/night) sits directly across the street from the neighborhood's main park. Head to the building's rooftop bar, The J. Parker, for some of the best cocktails and views in the city.

Best Neighborhood for Comedy Fans: Old Town

LA has movie stars, New York has SNL, but Chicago is where tons of giants in comedy—from John Belushi and Bill Murray to Tina Fey and Stephen Colbert—have gotten their start in the industry. And the best comedy in the city can be seen in the charming north-side 'hood of Old Town. It's home to both comedy institution The Second City as well as Zanies Comedy Club, a small venue that specializes in booking nationally renowned standup acts. And a quick walk down North Avenue gets you to the iO Theater, where you can catch some of the best improv comedy you'll ever see.

  • What to Do: This one's easy: go to a show at The Second City. The theater is home to three different stages, so tickets for a show are almost always available. After the show, head across the street to the Old Town Ale House, a cozy dive bar and late-night favorite of many Chicago comedians.

  • Where to Eat: Take a stroll down the tree-lined Sedgwick Street to Twin Anchors, a no-frills throwback that serves some of the best ribs in Chicago. The old-school joint was a favorite of Frank Sinatra, who loved the barbecue so much he would have it shipped to him while on the road.

  • Where to Stay: The Sofitel Magnificent Mile (from $72/night) is just a 15-minute bus ride away and even closer to the world-famous shopping strip.